Same user - same problem twice
I had a user in the late 1990's/early 2000's (a most unreasonable man and a director to boot) who caused me no end of troubles.
The first problem arose when he logged a call for a problem with Outlook freezing, not responding, et cetera.
Upon checking the machine and Outlook, I found that his pst file was close to 2GB in size (Windows 98 SE and Office 95). Turned out that about 90% of the size was taken up by his deleted items, so I told him what the problem was and if it was OK if I delete it, or should I copy it to another pst file should he want to keep it. The answer was "No - it is deleted."
About ten minutes later I had a frantic call from Head Office about this user's mail that I had deleted and that I should restore it immediately, as all his important stuff was gone. Luckily they backed me on this one when I had explained what the situation was (although he was sore with me for a long time about the incident and the fact that I could not recover his deleted items).
In order to prevent future occurrences I then gave him space on a server, where he could save his documents, and I wrote a little batch file that he could run at any time (provided Office was closed) to back up his documents as well as his pst's. I also stressed that he should run the file every Friday before calling it a day. So far so good.
Then he bought himself a copy of Windows XP towards the end of 2002 (as the company said that no machines would be upgraded to XP- only new machines would come with XP and machines would only be refreshed in the normal cycle. His laptop was also self-purchased, because the company did not buy laptops unless you really, REALLY needed one, and he NEEDED one).
So he logged a call for me to come and install XP NOW, as he needs it for an important meeting the next day. Once again my explanation that it would take about three days for the rebuild (cataloguing everything on the machine, getting his install disks for Office XP that he also bought, which was at home, as well as a number of other essential, cannot do without programs, then installing everything as well as the service pack that I had to download and install, and including a fairly generous contingency time to allow for possible problems) did not go down well, to say the least.
I vaguely remember that I was severely stressed for time, probably a slew of new machines I had to build (all new machines came naked and everything had to be installed by yours truly), which also did not help.
Stressing the importance of his running the backup script every day until the appointed installation time, since my having to do it would only stretch out the build time, and sending him an e-mail with all the details of what he needs to do beforehand and also apologising for the fact that he will have to make do with an old desktop in the time that his machine was out of commission, I was obviously left with a very grumpy guy.
Come the day of installation I installed his desktop and set it up for him, including copying my script and making sure that everything worked. The next question was whether he had done the backups as requested (to which the reply was that of course it had been done, just get out of the office and get cracking.
Come delivery time less than two days later, everything went swimmingly, until he started checking that everything was done correctly, only to query where his latest documents were. My insistence that everything that had been there had been restored, did not go down well. Upon checking, I saw that the last backup he had made was some months prior to the reinstall (I had no access to user's folders on the server - it was all tied to the users' domain accounts).
The upshot was that I had to remove his hard drive and take it to a professional outlet to try and recover as much as possible (he did lose a number of mail attachments, but luckily mostly non-important stuff - most of the other missing items could be recovered from the people who sent it to him or to whom he had sent it), since my e-mail regarding the rebuild did not explicitly mention the fact that he had to run the backup script and that everything that was on his hard disk would be lost forever. Plus I got a written warning for failing to ensure that no documents were lost.
------------------------------------------------------------------> What I felt like at the time.